As the chilly, fall weather grinds ceaselessly toward winter, unpleasant memories creep into my mind of slush, ice, frigid weather and short days. The season erodes my tolerance. So, for the next two columns, I’d like to propose novel destinations and ways for retirees to escape the worst of winter.

For our first inventive excursion, meet my friends Jack and Sophia (not their real names). Last year they spent three months on a cruise liner and they are doing it again. What’s the appeal?

“It’s absolutely effortless … there is zero stress. For as long as the cruise lasts, we live in the lap of luxury. No meals to prepare three times a day, no dishes to wash three times a day, no bags to schlep from one day to the next,” said Jack, now in his early 70s.

“We eat when we want—because we always take open seating—and we go on land if and when we want to,” Sophia said. It’s a non-regimented life with lots of entertainment at our disposal.”

“I like that aspect the best,” Jack agreed. “Moving to Florida in winter became regimented. It was like picking up and moving, lock stock and barrel, with everything you’re doing here, but in another place.

“On a ship you can knock yourself out with activities … there’s variety on board that doesn’t exist in an apartment in Florida.”

One routine they remain loyal to on land or sea is exercise; both are avid fitness enthusiasts.

Sophia, in her early 60s, was introduced to cruising only a few years ago when Jack took her on a short vacation to the Caribbean.

“Over the last few years, the dreariness of winter has become harder and harder to take,” said the South American native who encountered Montreal winters for the first time 10 years ago, after she met and married Jack. “There is not enough bright light during the day, so I feel like running away and hibernating. I find it very hard to motivate myself in winter.”

“And it’s perfect,” Jack added, “because I can’t take the cold. Being in the construction business for over 40 years, a lot of the time I had to build outdoors in winter to have everything ready for May. I’ve paid my dues.”

The couple compromised on which three months (December, January and February) to decamp for their cruise, which spanned half the globe. Jack and Sophia’s adventure provides an interesting prototype that you can shape to satisfy your own bucket list and as well as comply with your pocketbook.

“The trick is to find a ship that’s repositioning to kick start your plan into motion,” Jack said. “It also keeps the costs down. They (cruise companies) hate to have an empty ship when they are heading to pick up passengers’ so they lower the cost on that leg. Also, we don’t like taking large ships.”

The first part of their journey was a 39-day trip to Australia from San Diego on the Zaandam Holland America, which can accommodate 1,430 passengers, Jack’s ideal size. The ship was heading for Sydney to pick up passengers for its regular tour to Australia and Southeast Asia.

“Smaller ships can visit places where the ocean liners cannot. It’s like having your own yacht.”

Added Sophia: “We stopped in five ports in the South Pacific, including Hawaii. We toured the largest city, Honolulu, but we also visited an island where there were only 125 inhabitants.”

From Sydney, Jack and Sophia planned a self-designed jaunt to explore other parts of Australia, including Melbourne, Adelaide, Tasmania and Kangaroo Island. Travelers have to fly from place to place and take bus tours.

For more budget-inclined retirees, one insight garnered from their experience is that you can keep your expenses in check by avoiding flight and tour operators. In a metropolis like Sydney, there is much to enjoy by staying put until your boat sets sail.

After 15 days away from sea, they picked up the same ship in Sydney for a 14-day tour northward to nine ports along Australia’s coast, including Brisbane, Cairns, Darwin and the Great Barrier Reef.

Next, the MS Zaandam set sail for Southeast Asia, a floating hotel for another 30 days. Along the way, they visited ports and places in Singapore, Thailand, Jakarta, Bali, Vietnam, Cambodia, and finally ended up in Hong Kong—a sightseeing and shopping mecca—to catch their flight home after almost 100 days away.

They estimate the cost of their with-frills vacation at $50,000 for the two. “But you know,” Jack said, “if you go to Florida and rent an apartment for three months and if you take a real sharp pencil and add up all the costs, it’s not all that much more than a cruise.

“Maybe you’ll get an extra month or two of stay in Florida,” Sophia said. “You can’t compare that with what you get to see on a cruise.”

Next month, the couple begins their next escapade on the 1,258-person MS Maasdam, also a member of the Holland America fleet. They’ll stay on the same ship throughout their 99-day cruise, which will take them from Fort Lauderdale on a loop of the Caribbean, then sail from Fort Lauderdale to South America via the Caribbean.

Among other stops along the coast of Brazil, the ship will navigate the Amazon for a week before letting passengers off to enjoy the festivities of Rio de Janeiro’s Carnival.

Jack is already planning for their next winter’s adventure. “Only next year, the cruise is going to last 113 days,” he said with a smile.

Email mmedicoff@videotron to tell me where you’re planning to go for your three-month stay. For an upcoming edition of The Senior Times I look at Ecuador as an up-and-coming place to stay.